For me this is a simple assessment of risk/likelihood and consequences.
Having lived and work in the US I would say that the likelihood of something going wrong is pretty low. But that the risk increases if you’re not white, not middle class and not middle aged. The risk further increases if you are well travelled and have stamps in your passport form places the US doesn’t like.
On the consequences front, for a US citizen the consequences of a wrongful arrest or denied entry, while inconvenient, are short lived. For a non US citizen who is not protected by most of the rights set out in the US constitution the consequences of being stopped / pulled off the streets or denied entry are potentially a lot more serious. If you’re not white then they could be live changing.
So I’d make my assessment on whether to travel based on where I sat on that risk curve. Because I can control that, but I can’t control the consequences if the worst happens. If you are deemed as in the country illegally for whatever reasons you have almost no rights. I wouldn’t let the fact that it was a work or vacation trip make any difference;
if anything the risk going on a business trip is higher because you only need one agent to mis-interpret the reason for your trip as carrying out actual work rather than attending a meeting or conference to be in a whole world of visa pain. An ESTA wouldn’t cover you for actual work, but would a meeting or conference. Again, the risk is multiplied if you have any if the other factors mentioned above.
Those are my thought, as a recently retired professional who did for a while hold a green card and who has lived / worked in many countries over my working life. I know some EU countries do advise extra care when travelling to the US, so any reasonable employer should recognise if any of its staff are at higher risk.